1-para-dialkylaminoaryl-2.4-dialkyl-3-oxymethyl-5-pyrazolone.



I Ph.,D.,"and KARL STREITWO F, 'Ph. D., sub- ITEI) STATES PATENT OFFICE;

muriixtrcn STOLZ" AND KARL STREITWOLF, or. Hocnsr-oN-m -E-Mmnf GERMANY AssIGNoRs T0 FARBWERKE VORM. MEIs'rER LUCIUS & nnt nme, or HocHsT-on THE-MAIN, GERMANY, A CORPORATION OEGER'MANY.

1JARA-DIALKYIJAMINOABYLQ4-ZDIALKYL43-0XYMETHYL-5-PYRAZOLONE.

936,380. No Drawing.

Tb all whom it may iiimcem:

Be: it known that we, --FRI EDnIoH S'roLz,

jeets' of the Empire of Germany, residing at Hochst-on the-Main, Germany, have invent red certain: new and useful Improvements in li'Para Dialkylaminoaryl 2.4- Dialkyl 3 Oxymethyl-5-Pyiqazolones, of which the fol lowingisa specification.

[We have found hitherto unknown compounds which are Valuable on account of their antipyretic efliciency and" thejconstitution {of which corresponds to the formula mk i-n-u-(n'ar lki Naikyl Boom-(Q3 gumo the corresponding rationalifiterm' being '1- para dia lkylaminoaryl 42.4 diallryl 3-oxymethyl-5 pyra'zolones. These. new compounds may be produced by treating with alkylizing agents the p-am1noaryl-2A-dial- -hl-3roxymethyl-pyrazolones.

Theprocess may, forinstance, be 'c'arried out as follows The l-para-nitrophenyl-2.3.4-

trimethyl -'5 pyrazolone, crystallizing from benzene in the ,form of yellow leaflets and melting'zat 132, is obtained by treatingwith dim'ethyl-s'ulfate the lep-nitrophenyl-3. i-di produced by methyl-pyrazolone, this being condensing p nitrophenylhydrajzin with methylacetoacetic acid ester. tional' action of .onelmolecular proportion of brominand afterward of alkali on the first named pyrazolone the l para-nitrophenyl 2.4-di1nethyl-3-1bromomethyl-fi-pyra'zolone is obtainedwhich separates acid-in yellow crystals melting at 213-214". When the solution of the p-nitrophenyldi methylbromomethyl--pyrazolone in glacial acetic acid is boiled-with alkali acetate the acetic acidester 'ofthe 1-para-nitr0phenyl-- 2.4 dimethyl 3 oxyxhethyl-5-pyraz'olone is produced w-hich forms'yellow crystals melting at 163164 This" acetate-,I'when boiled with dilute sulfuric-1 acid, .is' decomposed yielding para 4 nitrophenyl 2.4 dimethyl-3- oxymethyl-5-pyrazolone which forms yellow "crystals melting at from 178-179".

L After reducin this nitroalcoholby means 0t tin and hy rochloric acid and after elimination of the tin by sulfur hydrogen from the solution, the latter is concentrated and then by adding a larger quantity of' sodium hy- Bythe addifrom glacial acetic .on adding ferric chlorid. '2. As a new product, the'l -para-dimethylpyrazolone,

, Sp t o s Patent Patented Oct. 12, 190 9. Application filed January 27,, 1909; Serial No. 474,557;

droxid the para-aminophenyI-2A dimethyl- 3-oxymethyl-5gpyrazolone is precipitated in the form of a crystallinepowder, This base crystallizes froin -hot water'in .the form of colorless prisms melting at 249 ;'it is diiiicultly-soluble in mostgf the organic solvents.

In an analogous manner homologous" paraaminophenyl 2,4, dimethyl 3-oxymethyl-5- pyrazolones can be produced, and their conversion 'into' the corresponding i dialkyla'zmin derivatives may be carried out by means of methyl iodid, but other -'methylating agents may also used.

Example; 5 parts by weight of l-p'araaminophenyl 2.4 dimethyl 3 oXymethyl-5- pyrazolone-are heated with Thereupon tlie alcohol is the residue dissolved in water. From this, solution, after being satu rated with caustic soda, the l-para-dimethylaminophenyl 2 4c-dimethyl-3-oxymethyl 5 pyrazolone is isolated by. extracting itby means of chloroformhi'lfhe residue remainingafter distilling olf the chloroform yields the purenew base by crystallization from water and alcohol. 7 Y l. I The l para dimethylaminophenyl 2 4 dimethyl 3 oxymethyl 5 pyrazolone is a -micro-crystalline white powder melting at -2 12 ,213.

I It is readily soluble in alcohol and chloroform, but diiiicultly soluble in cold water, benzene and ethyl acetate. When treated with hydrochloric acid it, forms a readily soluble hydroclrlorid, the solution of which is. of acid reaction and turns red when ferric chlorid is added.

Having now described our invention, what we claimis: 1. As new' 'products, the l-para-dialkyl: aminoaryl-24-dialkyl-3-oxymethyl 5 pyra- .zolones, which are 'whitecrystalline com pounds, melting at'temperatures above 150 being readily soluble" without decomposing, in alcohol and chloroform,- more diflicultly 3 parts of methyl iodid and 4 parts of methyl alcohol for 6 hours to 90*100". distilled 'ofi and soluble in cold water, forming when treated I with hydrochloric acid hydrochlorids which are readily soluble in waterandthe' solution of which is of acid reaction and turns red which is a white niorocrystalline compound, melting at 212-213" Without decomposing, being reiadll y iollublelin alcotures in'presence of two witnesses.

ho and chloroform, i 1011 t y so uble'in v cold Water, benzene and ethyl acetate, yield- 5 ing, when treated with hydrochloric acid, a i

readily soluble hydrochlorid the solution of \Vitnesses:

which is of acid reaction and turn s red on- JEAN GRUND,

adding ferric chlo'rid. I ,QARL GRUND.

. In testimony whereof, We-aflix our signa- 

